2-Chloro-6-methoxybenzoic acid → (2-Chloro-6-methoxyphenyl)methanol

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Reaction Steps

To a stirred solution of 2-chloro-6-(methyloxy)benzoic acid (0.252 g, 1.35 mmol, Arkpharminc) in dry THF (15 ml) at ambient temperature under nitrogen was added 1 M borane tetrahydrofuran complex (4.1 ml of solution in THF, 4.1 mmol, Aldrich) dropwise. The solution was then heated at reflux for 24 h and allowed to cool. The reaction mixture was quenched by the dropwise addition of methanol (4 ml), then heated at reflux for 30 min and allowed to cool. The solvent was removed in vacuo and the residue was partitioned between dilute aqueous ˜1M aqueous HCl and chloroform, the aqueous phase being extracted with more chloroform and the chloroform solutions being filtered through a phase separator. The combined chloroform solutions were evaporated in vacuo to give the title compound as a pale yellow solid (0.225 g); LCMS: (System 4) MH+=173, tRET=1.86 min.

Provenance & Evidence